Menu

Top 10 Best Hawaii Sailing Trips

Found 108 Sailing Trips activities in Hawaii. Sort by Popularity. - Page 2
 

Luxury Catamaran Whale Watch

(5 of 40 reviews)

From December through April, the waters off Maui come alive with the sights and sounds of the majestic humpback whales, and there’s no better way to witness the wonder than from the deck of our 65’ catamaran. This two-hour ex... More

Free Cancellation
Start From $159.00
 
Luxury Catamaran Whale Watch Likely to Sell Out

Luxury Catamaran Whale Watch

  • Hawaii
  • Superb40 reviews5

From December through April, the waters off Maui come alive with the sights and sounds of the majest....

    Free Cancellation
    Start From $159.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 702 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling a... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb702 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathta....

    Free Cancellation
    Start From $136.19
 
 

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

(4.8 of 259 reviews)

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos with the rainbow sails and also the beautiful scenery with Diamond head in the background. The net is also a fun ride and you’ll g... More

Free Cancellation
Start From $72.96
 
Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea Likely to Sell Out

Board from Waikiki Beach for a scenic Sunset Sail on the Hāwea

  • Hawaii
  • Superb259 reviews4.8

Our rainbow sails can be spotted from miles away. While on board you may capture such nice photos wi....

    Free Cancellation
    Start From $72.96
 
 

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

(4.7 of 807 reviews)

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beautiful coral reefs and tropical fish underneath the water, or bask in the warmth of paradise. From the experienced snorkeler to those... More

Free Cancellation
Start From $202.59
 
Four Winds Molokini Snorkeling Tour from Maalaea Harbor Likely to Sell Out

Four Winds Molokini Snorkeling Tour from Maalaea Harbor

  • Hawaii
  • Superb807 reviews4.7

Cruise to Molokini and snorkel into a crescent-shaped submerged volcanic crater! Discover the beauti....

    Free Cancellation
    Start From $202.59
 
 

Waikiki Sunset Boat Cruise

(5 of 64 reviews)

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed views create the best photo opportunities! Listen to great music as we cruise the Waikiki coastline with views of Diamond head cra... More

Free Cancellation
Start From $50.00
 
Waikiki Sunset Boat Cruise Likely to Sell Out

Waikiki Sunset Boat Cruise

  • Hawaii
  • Superb64 reviews5

No vacation is complete without experiencing a vibrant Hawaiian sunset from the water. Unobstructed ....

    Free Cancellation
    Start From $50.00
 
 

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

(5 of 178 reviews)

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designed for a comfortable ride in Hawaiian waters. What makes Hokulani unique from every other tour boat operating in Waikiki, is that s... More

Free Cancellation
Start From $79.00
 
Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming Likely to Sell Out

Best Waikiki Sunset Cruise:BYOB Sunset Sail with Swimming

  • Hawaii
  • Superb178 reviews5

Our vessel "Hokulani" is a beautiful and spacious custom built sailing trimaran specifically designe....

    Free Cancellation
    Start From $79.00
 
 

2-Hour Oahu Sunset Catamaran Sail

(4.9 of 112 reviews)

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran from the beautiful Ko Olina Marina on Oahu. Sip a cocktail and enjoy warm wind in your hair as you scan for dolphins and listen for... More

Free Cancellation
Start From $125.00
 
2-Hour Oahu Sunset Catamaran Sail Likely to Sell Out

2-Hour Oahu Sunset Catamaran Sail

  • Hawaii
  • Superb112 reviews4.9

Relax, sit back and delight in our 2-hour sunset sailing cruise on a gorgeous, 53' foot catamaran f....

    Free Cancellation
    Start From $125.00
 
 

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

(4.9 of 150 reviews)

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 21+ with valid ID to consume alcoholic beverages). Sail the south shore from Kaka'ako Waterfront to Waikiki, with beautiful views o... More

Free Cancellation
Start From $61.50
 
Honolulu Sunset Sail from Kewalo Harbor Including Drinks Likely to Sell Out

Honolulu Sunset Sail from Kewalo Harbor Including Drinks

  • Hawaii
  • Superb150 reviews4.9

Our Sunset Sail tour is a fun and wild 90-minute sail where all drinks are complimentary! (Must be 2....

    Free Cancellation
    Start From $61.50
 
 

Deluxe Sail & Snorkel to the Captain Cook Monument

(4.9 of 464 reviews)

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adventure will begin in the turquoise waters... More

Free Cancellation
Start From $179.27
 
Deluxe Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Deluxe Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb464 reviews4.9

Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient ....

    Free Cancellation
    Start From $179.27
 
 

Kona Tradewind Catamaran Day Sail

(4.8 of 40 reviews)

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunning Kona coastline. This relaxing daytime cruise is perfect for spotting Hawaii’s incredible marine wildlife—keep your eyes peel... More

Special Offer
Free Cancellation
Start From $99.96
(Saving 16% ) $119.00
 
-16% Kona Tradewind Catamaran Day Sail Likely to Sell Out

Kona Tradewind Catamaran Day Sail

  • Hawaii
  • Superb40 reviews4.8

Set sail aboard the spacious Honi Olani catamaran for a scenic 90-minute adventure along the stunnin....

    Special Offer
    Free Cancellation
    Start From $99.96
    (Saving 16% ) $119.00
 
 

Sunset Cocktail Cruise from Anaeho'omalu Bay

(4.8 of 60 reviews)

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohala Coast aboard our legendary sailing catamaran Seasmoke. This cruise includes unlimited soft drinks, tropical juices, beers, wines... More

Free Cancellation
Start From $165.00
 
Sunset Cocktail Cruise from Anaeho'omalu Bay Likely to Sell Out

Sunset Cocktail Cruise from Anaeho'omalu Bay

  • Hawaii
  • Superb60 reviews4.8

Enjoy the warm tropical breezes and unparalleled views of the Big Island as you sail along the Kohal....

    Free Cancellation
    Start From $165.00
 
 

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

(5 of 675 reviews)

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the horizon for dolphins and whales (seasonal) from our shaded cabin or sunny splash nets. Snorkel calm waters and lush coral gardens u... More

Free Cancellation
Start From $189.00
 
Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure Likely to Sell Out

Kealakekua Bay (Captain Cook Monument) Snorkel and Sail Adventure

  • Hawaii
  • Superb675 reviews5

Join us aboard our luxurious 50’ catamaran “Kona Style”, as we sail the Kona coast. Scan the h....

    Free Cancellation
    Start From $189.00
 
 

Afternoon Sail & Snorkel to the Captain Cook Monument

(4.9 of 245 reviews)

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtaking views of landscaped ledges of ancient lava flows. As you arrive at the "World Famous Captain Cook Monument" your snorkeling adve... More

Free Cancellation
Start From $136.19
 
Afternoon Sail & Snorkel to the Captain Cook Monument Likely to Sell Out

Afternoon Sail & Snorkel to the Captain Cook Monument

  • Hawaii
  • Superb245 reviews4.9

A three hour tour you won't want to miss! Set Sail down the Majestic Kona Coastline with breathtakin....

    Free Cancellation
    Start From $136.19
 
 

Sunset and Manta Ray Snorkel Adventure

(4.9 of 812 reviews)

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail the Kona coast, followed by the adventure of a lifetime - snorkeling with the majestic manta rays!  Upon arriving, receive an in... More

Free Cancellation
Start From $145.41
 
Sunset and Manta Ray Snorkel Adventure Likely to Sell Out

Sunset and Manta Ray Snorkel Adventure

  • Hawaii
  • Superb812 reviews4.9

Our most popular tour!  Watch a legendary Kona sunset from our spacious 50’ catamaran as you sail....

    Free Cancellation
    Start From $145.41
 
 

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

(4.7 of 147 reviews)

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well as ample seating and shade on board. Knowledgeable staff with plenty of interesting whale information Convenient location walking... More

Free Cancellation
Start From $79.00
 
Best Waikiki Whale Watching in Honolulu: Whales Guaranteed Likely to Sell Out

Best Waikiki Whale Watching in Honolulu: Whales Guaranteed

  • Hawaii
  • Superb147 reviews4.7

Guaranteed whale sightings* Spacious and modern Trimaran with unobstructed open air views as well a....

    Free Cancellation
    Start From $79.00
 
 

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

(4.8 of 154 reviews)

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamaran. Our Turtle Snorkeling Package offers a unique opportunity to snorkel with friendly turtles in the heart of Waikiki's picturesq... More

Free Cancellation
Start From $120.69
 
Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun Likely to Sell Out

Waikiki Catamaran Escape: Snorkel with Turtles & Water Sports Fun

  • Hawaii
  • Superb154 reviews4.8

Embark on a delightful journey through Oahu's pristine waters on a luxurious and comfortable catamar....

    Free Cancellation
    Start From $120.69
 
 

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure

(4.7 of 928 reviews)

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On Board Bar. When you trust Moana Sailing Co. for your snorkel adventure, you’re choosing the tour with the most professionalis... More

Free Cancellation
Start From $89.99
 
Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventure Likely to Sell Out

Moana’s Waikīkī Grand Guided Turtle Snorkel & Sailing Adventu....

  • Hawaii
  • Superb928 reviews4.7

Snorkel Turtle Canyon on the Largest Luxury Catamaran! Top Quality Gear, Certified Crew & Premium On....

    Free Cancellation
    Start From $89.99
 
 

Half-Day Deluxe Molokini Snorkel Excursion in Maui

(4.9 of 94 reviews)

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-renowned marine preserve home to over 400 species of tropical fish and coral reefs. Your adventure continues with a second snorkel... More

Free Cancellation
Start From $309.00
 
Half-Day Deluxe Molokini Snorkel Excursion in Maui Likely to Sell Out

Half-Day Deluxe Molokini Snorkel Excursion in Maui

  • Hawaii
  • Superb94 reviews4.9

Begin your morning with a chef-prepared buffet breakfast as we cruise to Molokini Crater, a world-re....

    Free Cancellation
    Start From $309.00
 
 

Waikoloa Catamaran Snorkel Sail Including Lunch

(4.6 of 98 reviews)

Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snorkeling cruise. As you head out across the clear Pacific waters, enjoy panoramic views of volcanic mountains, golden coastline, and ... More

Free Cancellation
Start From $169.00
 
Waikoloa Catamaran Snorkel Sail Including Lunch Likely to Sell Out

Waikoloa Catamaran Snorkel Sail Including Lunch

  • Hawaii
  • Superb98 reviews4.6

Sail the stunning Kona-Kohala Coast aboard a spacious catamaran on this unforgettable Waikoloa snork....

    Free Cancellation
    Start From $169.00
 
 

Snorkel with Manta Rays Guaranteed

(4.8 of 733 reviews)

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village. Travel Channel says “its one of the top ten things to do in your life time”, and Sea Paradise has been offering its guests th... More

Free Cancellation
Start From $141.57
 
Snorkel with Manta Rays Guaranteed Likely to Sell Out

Snorkel with Manta Rays Guaranteed

  • Hawaii
  • Superb733 reviews4.8

Join us aboard our luxurious catamaran, Hoku Nui, as we coast to the world famous Manta Ray Village.....

    Free Cancellation
    Start From $141.57
 
1 2 3 4 5
Booking.com
Booking.com
Booking.com